- Trapping bicyclic titanacyclopentenes with bis(trichloromethyl) carbonate (BTC): A new method to bicyclic cyclopentenones
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Bis(trichloromethyl) carbonate is found to trap bicyclic titanacyclopentenes providing a new method for bicyclization of enynes into bicyclic cyclopentenones.
- Zhao, Zongbao,Ding, Yu
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- On the mechanism of the palladium catalyzed intramolecular Pauson-Khand-Type reaction
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(Chemical Equation Presented) Density functional theory calculations and experimental studies have been carried out on the intramolecular Pauson-Khand-Type reaction mediated by a PdCl2-thiourea catalyst, which proceeds under mild reaction condi
- Lan, Yu,Deng, Lujiang,Liu, Jing,Wang, Can,Wiest, Olaf,Yang, Zhen,Wu, Yun-Dong
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- Formate as a CO surrogate for cascade processes: Rh-catalyzed cooperative decarbonylation and asymmetric Pauson-Khand-type cyclization reactions
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A rhodium-(S)-xyl-BINAP complex-catalyzed tandem formate decarbonylation and [2 + 2 + 1] carbonylative cyclization is described; this cooperative process utilizes formate as a condensed CO source, and the newly developed cascade protocol can be extended t
- Lee, Hang Wai,Chan, Albert S. C.,Kwong, Fuk Yee
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- Aqueous-phase, thermal Pauson-Khand reactions in the presence of surfactants
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Efficient stoichiometric Pauson-Khand reactions were realized in water as the only solvent, and in the presence of surfactants as additives. Use of the cationic surfactant CTAB provided good yields of cyclopentenones from the thermal reactions of pre-formed dicobalthexacarbonyl complexes of enynes and alkynes. The water-CTAB medium was found to be less effective with Co4(CO)12 as the promoter of the reaction. Incidentally, these results have provided a strictly water-based PKR protocol under very mild and convenient conditions.
- Krafft, Marie E.,Wright, James A.,Bo?aga, Llorente V. R.
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- Rhodium-catalyzed intramolecular Pauson-Khand reaction
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A rhodium dinuclear carbonyl complex, [RhCl(CO)2]2, serves as a catalyst of the intramolecular Pauson-Khand reaction. 1,6-Enynes are converted to cyclopentenone derivatives in high yield by heating in the presence of the catalyst und
- Koga, Yuji,Kobayashi, Toshitake,Narasaka, Koichi
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- Aqueous catalytic Pauson-Khand-type reactions of enynes with formaldehyde: Transfer carbonylation involving an aqueous decarbonylation and a micellar carbonylation
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One rhodium(I) complex catalyzes two processes in an overall Pauson-Khand-type reaction of enynes such as 1 with formaldehyde in an aqueous medium to give bicyclic cyclopentenones such as 2 in excellent yields. The use of a water-soluble phosphane ligand in conjunction with a hydrophobic phosphane ligand in the presence of a surfactant promotes the decarbonylation of formaldehyde in the aqueous phase and the carbonylation of enynes in the micellar phase.
- Fuji, Koji,Morimoto, Tsumoru,Tsutsumi, Ken,Kakiuchi, Kiyomi
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- Inhibition of enone reduction in aqueous-phase Pauson-Khand reactions
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NMO-promoted room temperature cyclizations of the cobalt carbonyl complexes of substrates bearing terminal and internal alkynes gave exclusively the Pauson-Khand (PK) reaction adducts in a water-Triton X-100 medium.
- Krafft, Marie E.,Wright, James A.,Bo?aga, Llorente V. R.
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- Glycerol - A non-innocent solvent for Rh-catalysed Pauson-Khand carbocyclisations
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Rh-catalysed carbocyclisations of the 1,6-enynes 1-8 efficiently gave bicyclo[3.3.0]octenones in neat glycerol. Unexpectedly, ligand-free [Rh(μ-OMe)(cod)]2 was highly selective. Moreover, TPPTS [tris(3-sulfonatophenyl)phosphane trisodium salt]
- Chahdoura, Faouzi,Dubrulle, Laurent,Fourmy, Kevin,Durand, Jerome,Madec, David,Gomez, Montserrat
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- Immobilized heterobimetallic Ru/Co nanoparticle-catalyzed Pauson-Khand-type reactions in the presence of pyridylmethyl formate
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Heterobimetallic Ru/Co nanoparticles, immobilized on charcoal, were synthesized and used as catalysts in the Pauson-Khand-type reaction in the presence of pyridylmethyl formate instead of carbon monoxide; the catalysts were effective for intra- and interm
- Park, Kang Hyun,Son, Seung Uk,Chung, Young Keun
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- Pauson-khand reactions in water
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We have investigated the cobalt mediated Pauson-Khand (PK) reaction in water. In the presence of detergents and surfactants, Co2(CO) 8 and Co4(CO)12 are effective under aqueous-phase, thermal PK reactions. In a
- Krafft, Marie E.,Wright, James A.,Bonaga, Llorente V.R.
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- Intramolecular Alkyne-Alkyne and Alkyne-Alkene Couplings Promoted by Iron Carbonyls
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The first examples of iron carbonyl-promoted intramolecular coupling of alkyne and alkene, giving rise to cyclopentenones, are described.
- Pearson, Anthony J.,Dubbert, Robert A.
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- Effect of lithium chloride on tuning the reactivity of Pauson-Khand reactions catalyzed by palladium-tetramethylthiourea
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A general and robust transition-metal-catalyzed Pauson-Khand reaction is still difficult to achieve. In this contribution, we describe our recent observations on the effect of lithium chloride on Pauson-Khand reactions catalyzed by palladium(II) chloride-
- Deng, Lu-Jiang,Liu, Jing,Huang, Ji-Qing,Hu, Yanhe,Chen, Mao,Lan, Yu,Chen, Jia-Hua,Lei, Aiwen,Yang, Zhen
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- Iridium-catalyzed cascade decarbonylation/highly enantioselective Pauson-Khand-type cyclization reactions
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An easily accessible chiral iridium-BINAP complex can effect the cooperative processes of decarbonylation of an aldehyde and cascaded enantioselective Pauson-Khand-type reaction. A survey of ligands revealed that atropisomeric aryl-diphosphine ligands wer
- Kwong, Fuk Yee,Lee, Hang Wai,Lam, Wai Har,Qiu, Liqin,Chan, Albert S.C.
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- Stable and Surface-active Co Nanoparticles Formed from Cation (x) Promoted Au/x-Co3O4 (x=Cs) as Selective Catalyst for [2+2+1] Cyclization Reactions
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Surface-active and highly stable cobalt nanoparticles generated from alkali ion-promoted gold catalyst for catalyzed carbonylative [2+2+1] cyclization reaction, is described. The gold nanoparticle‘s (AuNPs) role was assumed to dissociate the CO and H
- Oseghale, Charles O.,Mogudi, Batsile M.,Onisuru, Oluwatayo Racheal,Akinnawo, Christianah Aarinola,Fapojuwo, Dele Peter,Meijboom, Reinout
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- Iridium-catalyzed enantioselective Pauson-Khand-type reaction of 1,6-enynes
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Iridium-chiral diphosphine complex catalyzes an enantioselective intramolecular Pauson-Khand-type reaction to give various chiral bicyclic cyclopentenones. The enantioselective reaction proceeds more smoothly and enantioselectively under a lower partial p
- Shibata, Takanori,Toshida, Natsuko,Yamasaki, Mitsunori,Maekawa, Shunsuke,Takagi, Kentaro
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- SeO2-Mediated Oxidative Transposition of Pauson-Khand Products
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Oxidative transpositions of bicyclic cyclopentenones mediated by selenium dioxide (SeO2) are disclosed. Treatment of Pauson-Khand reaction (PKR) products with SeO2 in the presence or absence of water furnishes di- and trioxidized cyclopentenones, respectively. Mechanistic investigations reveal multiple competing oxidation pathways that depend on substrate identity and water concentration. Functionalization of the oxidized products via cross-coupling methods demonstrates their synthetic utility. These transformations allow rapid access to oxidatively transposed cyclopentenones from simple PKR products.
- Dibrell, Sara E.,Maser, Michael R.,Reisman, Sarah E.
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supporting information
p. 6483 - 6487
(2020/04/30)
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- Rhodium(i)-catalyzed Pauson-Khand-type reaction using formic acid as a CO surrogate: An alternative approach for indirect CO2 utilization
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Formic acid is found to be an ideal CO surrogate for the rhodium(i)-catalyzed Pauson-Khand-type (PK-type) reaction of various substituted 1,6-enynes to afford bicyclic cyclopentenones in moderate to good yields. High TON value of up to 263 and good results in the gram-scale experiment were also obtained, demonstrating the efficacy of this methodology. In addition, heterocyclic molecules of pharmaceutical importance were also furnished via inter- or intra-molecular hetero-PK-type reactions, further broadening the application of current strategy. In this protocol, formic acid was utilized as a bridging molecule for the conversion of CO2 to CO, since formic acid is manufactured via catalytic hydrogenation of CO2 and releases CO in the presence of acetic anhydride readily. Therefore, this methodology represents a green and indirect approach for chemical valorization of CO2 in the preparation of value-added compounds.
- Lang, Xian-Dong,You, Fei,He, Xing,Yu, Yi-Chen,He, Liang-Nian
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p. 509 - 514
(2019/02/14)
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- Integration of co2 reduction with subsequent carbonylation: Towards extending chemical utilization of co2
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Currently, it still remains a challenge to amplify the spectrum of chemical fixation of CO2, although enormous progress has been achieved in this field. In view of the widespread applications of CO in a myriad of industrial carbonylation processes, an alternative strategy is proposed in which CO2 reduction to CO is combined with carbonylation with CO generated ex situ, which affords efficiently pharmaceutically and agrochemically attractive molecules. As such, CO2 in this study was efficiently reduced by triphenysilane using CsF to CO in a sealed two-chamber reactor. Subsequently, palladium-catalyzed aminocar-bonylation, carbonylative Sonogashira coupling of aryl iodides, and rhodium(I)-mediated Pauson–Khand-type reaction proceeded smoothly to yield amides, alkynones, and bicyclic cy-clopentenones, respectively. Furthermore, the formed alkynones can further be successfully converted to a series of heterocycles, for example, pyrazoles, 3a-hydroxyisoxazolo[3,2-a]isoindol-8-(3aH)-one derivatives and pyrimidines in moderate yields. The striking features of this protocol include operational simplicity, high efficiency, and relatively broad application scope, which represents an alternative avenue for CO2 transformation.
- Lang, Xian-Dong,He, Liang-Nian
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- A catalytic scalable Pauson-Khand reaction in a plug flow reactor
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A catalytic, scalable intra- and intermolecular Pauson-Khand reaction protocol using generally 5 mol% of Co2(CO)8 as the catalyst in a plug flow reactor (PFR) is shown.
- García-Lacuna, Jorge,Domínguez, Gema,Blanco-Urgoiti, Jaime,Pérez-Castells, Javier
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supporting information
p. 4014 - 4017
(2017/04/11)
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- Intramolecular Pauson-Khand reaction catalyzed by oxime-derived palladacycles
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Oxime-derived palladacycles were successfully applied as a novel class of catalysts in the intramolecular Pauson-Khand reactions. Allylpropargyl ethers and allylpropargyl amines can be efficiently converted to the cyclopentenone products with good to exce
- Wang, Xue-Rui,Lu, Fu-Hua,Song, Yang,Lu, Zhong-Lin
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supporting information; experimental part
p. 589 - 592
(2012/02/01)
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- Rh(I)-catalyzed cyclocarbonylation of enynes with glyceraldehyde: An available carbonyl source derived from sugar alcohols
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Catalytic cyclocarbonylation reactions using a glyceraldehyde derivative as a carbonyl source are described. The rhodium(I)-catalyzed reaction of enynes with glyceraldehyde acetonide gave bicyclic cyclopentenones as the products. This presents an interesting use of a sugar alcohol derived carbon resource as well as a convenient procedure for the cyclocarbonylation of enynes. Georg Thieme Verlag Stuttgart · New York.
- Ikeda, Keiichi,Morimoto, Tsumoru,Tsumagari, Takayuki,Tanimoto, Hiroki,Nishiyama, Yasuhiro,Kakiuchi, Kiyomi
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supporting information; scheme or table
p. 393 - 396
(2012/03/27)
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- Hydrogen-activated benzylidynetricobalt nonacarbonyl: Carbonylative cyclization of enynes in synthesis gas without reducing substrates and products
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Benzylidynetricobalt nonacarbonyl was activated by hydrogen and catalyzed the carbonylative cyclization of enynes without reducing substrates and products. The Japan Institute of Heterocyclic Chemistry.
- Sugihara, Takumichi,Wakabayashi, Akihito,Nishizawa, Mugio,Honzawa, Shinobu
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scheme or table
p. 1189 - 1194
(2011/05/05)
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- Cobalt oxide supported gold nanoparticles as a stable and readily-prepared precursor for the in situ generation of cobalt carbonyl like species
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A treatment of cobalt oxide supported gold nanoparticles (Au/Co 3O4) under syngas atmosphere effectively generated a cobalt carbonyl-like active species in the reaction vessel. The preparation of Au/Co3O4 was quite simple and the in situ generated cobalt species could be used as a stable and easy handling alternative for dicobalt octacarbonyl without bothersome purification prior to use. The reactions, which are sensitive to the purity of the dicobalt octacarbonyl, such as the alkoxycarbonylation of epoxides and the Pauson-Khand reaction, smoothly progressed with Au/Co3O4.
- Hamasaki, Akiyuki,Muto, Akiko,Haraguchi, Shingo,Liu, Xiaohao,Sakakibara, Takanori,Yokoyama, Takushi,Tokunaga, Makoto
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supporting information; experimental part
p. 6869 - 6872
(2012/02/05)
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- Utilization of aldoses as a carbonyl source in cyclocarbonylation of enynes
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Figure presented. The reaction of enynes with acetyl-masked aldoses in the presence of a rhodium(I) catalyst resulted in cyclocarbonylation, thus avoiding the direct use of carbon monoxide, to afford bicyclic cyclopentenones. In rhodium catalysis, aldoses serve as a carbon monoxide equivalent by donating their carbonyl moieties on the acyclic aldehyde form to enynes. A variety of aldoses, including d-glucose, d-mannose, d-galactose, d-xylose, and d-ribose, can be used as a carbonyl source. Using the method, a wide variety of enynes were cyclocarbonylated in 22-67% yields. An asymmetric variant also proceeded with moderate to high enantioselectivity.
- Ikeda, Keiichi,Morimoto, Tsumoru,Kakiuchi, Kiyomi
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supporting information; experimental part
p. 6279 - 6282
(2010/12/25)
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- Rhodium-catalyzed pauson-khand-type reaction using alcohol as a source of carbon monoxide
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Three in one pot! Bicyclic cyclopentenones have been synthesized from enynes in alcohol in the presence of a rhodium catalyst through a newly developed auto-tandem catalytic reaction. This process combines three mechanistically distinctive reactions - an
- Park, Ji Hoon,Cho, Yoonhee,Chung, Young Keun
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supporting information; experimental part
p. 5138 - 5141
(2010/10/03)
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- Microwave-assisted rhodium-complex-catalyzed cascade decarbonylation and asymmetric Pauson-Khand-type cyclizations
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Microwave-assisted Rh-diphosphane-complex-catalyzed dual catalysis is reported. This cooperative process provides [2+2+1] cycloadducts by sequential decarbonylation of aldehyde or formate and carbonylation of enynes within a short period of time. Various
- Hang, Wai Lee,Lai, Na Lee,Chan, Albert S. C.,Fuk, Yee Kwong
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scheme or table
p. 3403 - 3406
(2009/04/07)
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- An efficient catalytic protocol for the Pauson-Khand reaction
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New experimental conditions have been developed for an efficient catalytic Pauson-Khand reaction. These are based on the use of a mixture of molecular sieves and tert-butanol as inducers of the process. This mixture, with the appearance of a paste, is abl
- Blanco-Urgoiti, Jaime,Abdi, Delbrin,Domínguez, Gema,Pérez-Castells, Javier
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- Rh-catalyzed aqueous pauson-khand-type cycloaddition in microwave-irradiated medium
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Microwave-assisted Rh-catalyzed dual catalysis in aqueous medium is described. This tandem process transforms the enyne to cycloadduct by cascade decarbonylation of formate ester and subsequently carbonylation of enyne under microwave-irradiated condition
- Lee, Hang Wai,Kwong, Fuk Yee,Chan, Albert S. C.
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experimental part
p. 1553 - 1556
(2009/04/07)
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- Enantioselective preparation of 1,1-diarylethanes: Aldehydes as removable steering groups for asymmetric synthesis
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Cut it out! Convenient procedures have been delineated for the synthesis of optically active, functionalized 1,1-diaryl-ethanes by decarbonylation of β,β-diaryl-propionaldehydes. The process can be conducted as a one-pot 1,4-addition/decarbonylation sequence. Aldehydes are used as removable steering groups in this new strategy for the preparation of optically active building blocks. (Chemical Equation Presented)
- Fessard, Thomas C.,Andrews, Stephen P.,Motoyoshi, Hajime,Carreira, Erick M.
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p. 9331 - 9334
(2008/12/21)
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- Tetramethyl thiourea/Co2(CO)8-catalyzed Pauson-Khand reaction under balloon pressure of CO
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(Chemical Equation Presented) A Pauson-Khand type of conversion of enynes to bicyclic cyclopentenones employing the commercially available Co 2(CO)8 and tetramethylthiourea (TMTU) as catalysts is described. This method allows a varie
- Tang, Yefeng,Deng, Lujiang,Zhang, Yandong,Dong, Guangbin,Chen, Jiahua,Yang, Zhen
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p. 593 - 595
(2007/10/03)
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- Immobilized Co/Rh heterobimetallic nanoparticle-catalyzed Pauson-Khand-type reaction
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Co/Rh heterobimetallic nanoparticles were prepared from cobalt-rhodium carbonyl clusters [Co2Rh2(CO)12 and Co 3Rh(CO)12] and immobilized on charcoal. HR-TEM revealed that the size of the heterobimetal
- Kang, Hyun Park,Young, Keun Chung
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p. 854 - 866
(2007/10/03)
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- Thioureas as ligands in the Pd-catalyzed intramolecular Pauson-Khand reaction
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(Chemical Equation Presented) The thiourea-Pd complex was established as a novel type of catalyst in the PKR of allylpropargylamine, and the demonstrated chemistry may prove to be valuable for developing thiuorea as a ligand for the Pd-catalyzed Pauson-Kh
- Tang, Yefeng,Deng, Lujiang,Zhang, Yangdong,Dong, Guangbin,Chen, Jiahua,Yang, Zhen
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p. 1657 - 1659
(2007/10/03)
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- Pauson-Khand reactions catalyzed by entrapped rhodium complexes
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An entrapped Rh complex prepared by a sol-gel process has been used as a catalyst in the Pauson-Khand reaction under mild reaction conditions; the catalyst is easily recovered and reused at least 10 times without losing catalyst activity.
- Park, Kang Hyun,Son, Seung Uk,Chung, Young Keun
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p. 2827 - 2830
(2007/10/03)
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- Cobalt Nanoparticles on Charcoal: A Versatile Catalyst in the Pauson-Khand Reaction, Hydrogenation, and the Reductive Pauson-Khand Reaction
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(Matrix Presented) Dispersions of nanometer-sized cobalt particles with very high stability were prepared in charcoal and analyzed by electron microscopy and X-ray analysis. The resulting cobalt nanoparticles on charcoal (CNC) were successfully used as a catalyst for the carbonylative cycloaddition of alkyne, alkene, and carbon monoxide (Pauson-Khand reaction), hydrogenation, and the reductive Pauson-Khand reaction.
- Son, Seung Uk,Park, Kang Hyun,Chung, Young Keun
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p. 3983 - 3986
(2007/10/03)
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- The first intramolecular pauson-khand reaction in water using aqueous colloidal cobalt nanoparticles as catalysts
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Chemical equation presented The first intramolecular Pauson-Khand reaction in water was successfully carried out by using aqueous colloidal cobalt nanoparticles as catalysts.
- Son, Seung Uk,Lee, Sang Ick,Chung, Young Keun,Kim, Sang-Wook,Hyeon, Taeghwan
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p. 277 - 279
(2007/10/03)
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- Rhodium complex-catalyzed Pauson-Khand-type reaction with aldehydes as a CO source
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With aldehydes as a CO source under solvent-free conditions, rhodium complex efficiently catalyzed an intramolecular carbonylative alkene-alkyne coupling (Pauson-Khand-type reaction) and various bicyclic enones were obtained in high yield. Experiments und
- Shibata, Takanori,Toshida, Natsuko,Takagi, Kentaro
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p. 7446 - 7450
(2007/10/03)
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- CO-transfer carbonylation reactions. A catalytic pauson-khand-type reaction of enynes with aldehydes as a source of carbon monoxide
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The reaction of enynes with aldehydes in the presence of a catalytic amount of [RhCl(cod)]2/dppp results in the Pauson-Khand-type reaction without the use of gaseous carbon monoxide to give bicyclic cyclopentenones in high yields (14 examples).
- Morimoto, Tsumoru,Fuji, Koji,Tsutsumi, Ken,Kakiuchi, Kiyomi
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p. 3806 - 3807
(2007/10/03)
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- Catalytic Pauson - Khand-Type Reaction Using Aldehydes as a CO Source
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(matrix presented) Rhodium complex-catalyzed carbonylative alkene-alkyne coupling proceeds using aldehydes as a CO source. Cinnamaldehyde is the best CO donor, and various cyclopentenones were provided in high isolated yields by a solvent-free system.
- Shibata, Takanori,Toshida, Natsuko,Takagi, Kentaro
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p. 1619 - 1621
(2007/10/03)
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- The rhodium-catalyzed Pauson-Khand reaction
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A rhodium carbonyl complex, [RhCl(CO)2]2, serves as a catalyst of the intra- and inter-molecular Pauson-Khand reaction. By the use of the rhodium catalyst, cyclopentenone derivatives are prepared from various 1,6- and 1,7-enynes unde
- Kobayashi, Toshitake,Koga, Yuji,Narasaka, Koichi
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- Colloidal cobalt nanoparticles: A highly active and reusable Pauson-Khand catalyst
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A new Pauson-Khand catalyst based on colloidal cobalt nanoparticles has been developed; the catalyst is highly effective for many intra- and inter-molecular Pauson--Khand reactions and can be recycled and reused many times without losing catalytic activit
- Kim,Uk Son,Seong Lee,Hyeon,Keun Chung
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p. 2212 - 2213
(2007/10/03)
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- Phosphane sulfide/octacarbonyldicobalt-catalyzed Pauson - Khand reaction under an atmospheric pressure of carbon monoxide
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Convenient access to cyclopentenones is provided by catalytic intra- and intermolecular Pauson - Khand reactions in the presence of octacarbonyldicobalt and tributylphosphane sulfide. In contrast to other reactions of this type, they proceed under mild co
- Hayashi, Minoru,Hashimoto, Yukihiko,Yamamoto, Yoji,Usuki, Junji,Saigo, Kazuhiko
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p. 631 - 633
(2007/10/03)
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- Scope of the intramolecular titanocene-catalyzed Pauson-Khand type reaction
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A Pauson-Khand type conversion of enynes to bicyclic cyclopentenones employing the commercially available precatalyst titanocene dicarbonyl is described. This methodology shows excellent functional group tolerance for a group 4 metallocene-catalyzed process. The scope and limitations of this cyclization with respect to 1,6-, 1,7- and 1,8-enynes with a variety of terminal alkyne substituents, chiral enynes, and enynes containing substituted olefins are described in detail. A mechanism involving carbonylation of an intermediate titanacyclopentene has been proposed.
- Hicks, Frederick A.,Kablaoui, Natasha M.,Buchwald, Stephen L.
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p. 5881 - 5898
(2007/10/03)
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- Bicyclization of enynes using the Cp2TiCl2-Mg-BTC system: A practical method to bicyclic cyclopentenones
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Bicyclic titanacycles 2 generated with the Cp2TiCl2-Mg-P(OEt)3 system can be trapped with bis(trichloromethyl) carbonate (BTC) to give bicyclic cyclopentenones 3 in good yields. The titanacycle 2m was isolated and well- identified. Bicyclization of enynes containing 1,2-disubstituted olefin by this method gave good results with excellent stereoselectivity.
- Zhao, Zongbao,Ding, Yu,Zhao, Gang
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p. 9285 - 9291
(2007/10/03)
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- Rate Enhancement of the Pauson-Khand Reaction by Primary Amines
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Keywords: alkyne complexes; amines; carbonyl complexes; cobalt; cyclization
- Sugihara, Takumichi,Yamada, Mamiko,Ban, Hitoshi,Yamaguchi, Masahiko,Kaneko, Chikara
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p. 2801 - 2804
(2007/10/03)
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- A practical titanium-catalyzed synthesis of bicyclic cyclopentenones and allylic amines
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A practical titanium-catalyzed synthesis of bicyclic cyclopentenones and allylic amines is described. The process converts enyne substrates to iminocyclopentenes using 10 mol % of the air- and moisture-stable precatalyst Cp2TiCl2 in the presence of n-BuLi and triethylsilyl cyanide. The resulting iminocyclopentenes can be hydrolyzed to cyclopentenones in good yields or reduced to allylic silylamines with Red-Al or DIBALH. Treatment of the crude silylamines with acetyl chloride allows isolation of allylic amides in excellent yields.
- Hicks, Frederick A.,Berk, Scott C.,Buchwald, Stephen L.
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p. 2713 - 2718
(2007/10/03)
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